Methyl 1-(2,4-dimethylphenyl)sulfonylpiperidine-4-carboxylate | 1095349-92-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 1-(2,4-dimethylphenyl)sulfonylpiperidine-4-carboxylate
• CAS: 1095349-92-0
• 化学式: C₁₅H₂₁NO₄S
• 分子量: 311.402
• InChiKey: DLHUIEUABFXKAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 1-(2,4-dimethylphenyl)sulfonylpiperidine-4-carboxylate 在 4-二甲氨基吡啶 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 1-(2,4-dimethylphenyl)sulfonyl-N-phenylpiperidine-4-carboxamide
  参考文献：
  名称：

  Synthesis and structure–activity relationship of piperidine-derived non-urea soluble epoxide hydrolase inhibitors

  摘要：

  A series of potent amide non-urea inhibitors of soluble epoxide hydrolase (sEH) is disclosed. The inhibition of soluble epoxide hydrolase leads to elevated levels of epoxyeicosatrienoic acids (EETs), and thus inhibitors of sEH represent one of a novel approach to the development of vasodilatory and anti-inflammatory drugs. Structure-activities studies guided optimization of a lead compound, identified through high-throughput screening, gave rise to sub-nanomolar inhibitors of human sEH with stability in human liver microsomal assay suitable for preclinical development. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.11.084
• 作为产物：
  描述：

  4-哌啶甲酸甲酯 、 2,4-二甲基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到Methyl 1-(2,4-dimethylphenyl)sulfonylpiperidine-4-carboxylate
  参考文献：
  名称：

  Synthesis and structure–activity relationship of piperidine-derived non-urea soluble epoxide hydrolase inhibitors

  摘要：

  A series of potent amide non-urea inhibitors of soluble epoxide hydrolase (sEH) is disclosed. The inhibition of soluble epoxide hydrolase leads to elevated levels of epoxyeicosatrienoic acids (EETs), and thus inhibitors of sEH represent one of a novel approach to the development of vasodilatory and anti-inflammatory drugs. Structure-activities studies guided optimization of a lead compound, identified through high-throughput screening, gave rise to sub-nanomolar inhibitors of human sEH with stability in human liver microsomal assay suitable for preclinical development. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2012.11.084

文献信息

• POTENT NON-UREA INHIBITORS OF SOLUBLE EPOXIDE HYDROLASE
  申请人：The Trustees of Columbia University in the City of New York

  公开号：US20140336193A1

  公开（公告）日：2014-11-13

  The present invention relates to compounds that exhibit vasodilatory and anti-inflammatory effects by inhibiting the activity of soluble epoxide hydrolase (sEH). The present invention is also directed to methods of identifying such compounds, and use of such compounds for the treatment of diseases related to dysfunction of vasodilation, inflammation, and/or endothelial cells. In particular non-limiting embodiments, components of the invention may be used to treat hypertension.
• Synthesis and structure–activity relationship of piperidine-derived non-urea soluble epoxide hydrolase inhibitors
  作者：Stevan Pecic、Svetlana Pakhomova、Marcia E. Newcomer、Christophe Morisseau、Bruce D. Hammock、Zhengxiang Zhu、Alison Rinderspacher、Shi-Xian Deng

  DOI：10.1016/j.bmcl.2012.11.084

  日期：2013.1

  A series of potent amide non-urea inhibitors of soluble epoxide hydrolase (sEH) is disclosed. The inhibition of soluble epoxide hydrolase leads to elevated levels of epoxyeicosatrienoic acids (EETs), and thus inhibitors of sEH represent one of a novel approach to the development of vasodilatory and anti-inflammatory drugs. Structure-activities studies guided optimization of a lead compound, identified through high-throughput screening, gave rise to sub-nanomolar inhibitors of human sEH with stability in human liver microsomal assay suitable for preclinical development. Published by Elsevier Ltd.